The McCormack reaction is a method for the synthesis of

organophosphorus compound Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...

s. In this reaction, a 1,3-

diene In organic chemistry, a diene ( ); also diolefin, ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nome ...

and a source of R₂P⁺ are combined to give phospholenium cation. The reaction is named after W. B. McCormack, a research chemist at duPont. An illustrative reaction involves phenyldichlorophosphine and

isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers ar ...

: :

The reaction proceeds via a

pericyclic In organic chemistry, a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and the bond orbitals involved in the reaction overl ...

+4process. The resulting derivatives can be hydrolyzed to give the

phosphine oxide Phosphine oxide is the inorganic compound with the formula H3PO. Although stable as a dilute gas, liquid or solid samples are unstable. Unlike many other compounds of the type POxHy, H3PO is rarely discussed and is not even mentioned in major so ...

Dehydrohalogenation In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate (chemistry), substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogen ...

gives the

phosphole Phosphole is the organic compound with the chemical formula ; it is the phosphorus analog of pyrrole. The term phosphole also refers to substituted derivatives of the parent heterocyclic compound, heterocycle. These compounds are of theoretical in ...

.Handbook of organophosphorus chemistry by Robert Engel, CRC Press, 1992. {{ISBN, 0-8247-8733-1.

References

Cycloadditions Cheletropic reactions Name reactions